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Molecules 2011, 16(11), 9755-9763; doi:10.3390/molecules16119755
Article

Synthesis of Methacrylate Monomers with Antibacterial Effects Against S. Mutans

1,2,3,* , 4, 5, 1,2 and 1,2
1 Department of Biomaterials Science, Institute of Dentistry and Biocity Turku Biomaterial Research Program, University of Turku, Turku 20520, Finland 2 Turku Clinical Biomaterials Centre-TCBC, University of Turku, Turku 20520, Finland 3 College of Materials Science and Engineering, South China University of Technology, Guangzhou 510641, China 4 Institute of Dentistry, University of Turku, Turku 20520, Finland 5 Antimicrobial Resistance Unit, National Institute for Health and Welfare, Turku 20520, Finland
* Author to whom correspondence should be addressed.
Received: 18 October 2011 / Revised: 21 November 2011 / Accepted: 22 November 2011 / Published: 23 November 2011
(This article belongs to the Section Medicinal Chemistry)
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Abstract

A series of polymerizable quaternary ammonium compounds were synthesized with the aim of using them as immobilized antibacterial agents in methacrylate dental composites, and their structures were characterized by FT-IR, 1H-NMR, and 13C-NMR analysis. Their antibacterial activities against the oral bacterium Streptococcus mutans were evaluated in vitro by a Minimum Inhibitory Concentration test, and the results showed that 2-dimethyl-2-hexadecyl-1-methacryloxyethyl ammonium iodide (C16) had the highest antibacterial activity against S. mutans, and 2-dimethyl-2-pentyl-1-methacryloxyethyl ammonium iodide (C5) and 2-dimethyl-2-octyl-1-methacryloxyethyl ammonium iodide (C8) did not show any inhibition.
Keywords: dental materials; methacrylate; quaternary ammonium compounds; antibacterial dental materials; methacrylate; quaternary ammonium compounds; antibacterial
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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He, J.; Söderling, E.; Österblad, M.; Vallittu, P.K.; Lassila, L.V.J. Synthesis of Methacrylate Monomers with Antibacterial Effects Against S. Mutans. Molecules 2011, 16, 9755-9763.

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